Water-insoluble azo dyestuff



Patented Oct. 9, 1934 1,976,187;

. 1,976,187 WATER-INSOLUBLE Azo DYESTUFF Wilhelm Neelmeier, Leverkusen, and Wilhelm Lamberz, Leverkusen-Wiesdorf, Germany, assignors to General Aniline Works," Inc., New York, N. Y., a corporation of Delaware No Drawing. Application August 10, 1932, Serial No. 628,227 In Germany September 8, 1931 14 Claims. (Cl. 260-95) The present invention relates to new Water- EXAMPLE 1 insoluble dyestufis and to fibers dyed with said dyestuffs, more particularly it relates to azo dye- Gmundmg bath stuffs which maybe represented by the probable 4 grams of 2.3-hydroxynaphthoyl-l'-aminogeneral formula: 2'-4'-dimethoxy-5-chlorobenzene are dissolved R1 in a mixture of 8 cos. of denatured alcohol, 2 cos. \NAMFQOOH of aqueous caustic soda lye of 38 B., 4 cos. of

, z Water, 4 cos. of aqueous bone glue solution 1:10 N and 4 cos. of aqueous formaldehyde of 33% l0; strength. The solution is stirred into about half N a liter of water containing 10 cos. of aqueous caustic soda lye of 38 B., 6 cos. of Turkey red oil and 2 grams of bone glue. The solution thus obtained is made up with water to one liter.

3o above, and coupling with 2.3-

- 35 fiber according to the known method of preparing Developing bath f 2.6 grams of 1-methoxy-2-aminobenzene-4- wherein R1 and R2 stand for alkyl or aralkyl in sulfodiethylamide are dissolved with 25 cos. of such a manner that R1 and R2 together contain warm water and 3 cos. of aqueous hydrochloric .0 at least 3 carbon atoms. acid of 20 B. The solution is cooled to about Our new dyestuffs areobtainable by diazotizing 15 0., and 0.75 grams of sodium nitrite of 98% in the usual manner an'aromatic amine of the strength dissolved in some Water are stirred in. general formula: After about 10 minutes the excess hydrochloric R1 acid is neutralized by the addition of sodiumacetate, 50 grams of common salt are added, and g the solution is made up with Water to one liter.

NOgS 0011a A R2 I NH: Dyeing directions Wherem R1 and R2 mean the, am as stated 50 grams of well-boiled cotton yarn are introhydroxynaphthoy duced for about half an hour into the grounding 99 bath at a temperature of 30 C.,-well squeezed and introducedfor about half an hour into the developing bath, rinsed, soaped in a boiling bath,

rinsed again anddried. Thus is obtained a clear 9 Turkey red dyeing of good 'fastness to light, 5

ice colors generally yield Turkey red shades of g g chlorine, Washing and boiling in soda and caustic good iastness to light, weather, chlorine, and soda; 1 I I a V boiling in aqueous caustic soda. Especially valu- 4 I able are those dyestuffs which havebeen pre- The dyestufi has the fonvowmvg formula l'-amino-2-4'-dimethoxy 5 chlorobenzene in substance or on the fiber.

Ourdyestufis prepared in substance are generally red powders,'the dyestuffs prepared on the 0 pared with such bases in which the hydrogen of 100 4s from 1 to 4 carbon atoms. O1

50 ethylamine or from Z-nitro-l-chlorobenzene-4- the sulfamide radical is substituted by aliphatic radicals containing together. 3 to 8 carbon atoms, V L Q0131 or by two radicals :ofthe benzyl series, or by one radical of the benzyl series and one alkyl group The bases'used in our process are obtainable, for example, by treating according to customary 05:0 methods 2-nitroanisol-4-sulfodiethyl-amide (obtainable from Z-nitroanisol sulfochloride and di- HNO0 sulfodiethylamide and methanol) with a reducing .b agent. A further process of manufacture of the base is by treating 2-acetanisidine-4-sulfochloride In the followingtable further bases are indi- (obtainable from 2-acetanisidine-4-sulfonic acid cated falling within'the' scope of our invention,

.55 according to known methods) with diethylamine yielding when diazotized and coupled on the fiber a 50 thereto:

and saponifying the 2-acetanisidine-4-sulfowith 2.3-hydroxynaphthoyl-l'-amino-2.4'-dime- :diethylamide obtained. thoxy-5-ch-lorobenzene Turkey red shades of The inventionis further illustrated by the good fastness to-chlorine, washing and boiling in following examples without being restricted soda and caustic soda, combined with good fastness to light:

l-amino-2-methoxy-S-suIfo-di-n-propylamide,

l-amino-2-methoxy 5 sulfo-methyl-n-butylamide,

l-amino-Z-methoxy-S-sulfo ethyl-n-butylam ide,

1-amino-2-methoxy-5- sulfo methyl -iso,hutylamide,

l-amino-2-methoxy-5-sulio-methyl n amylamide,

1 -amino-2- methoxy 5 sulfo-n-butyl-isobutylamide,

l amino-Z-methoxy 5 sulfo-di-isobutylamide,

1-amino-2-methoXy-5 sulfo -namyl-isocaprylamide,

EXAMPLE 2 2.6 parts by weight of l-methoxy-Z-aminobenzene--sulfonic acid diethylamide are diazotized in the usual manner. The diazo solution, is coupled with a solution of 3.6 parts by weight of 2.3-hydroxy-carboylnapthalene-1'-amino-2.4'- dimethoxy-S-chloro-benzene in dilute aqueous caustic soda lye and Turkey red oil, to which has been added a quantity of sodium acetate sufficient for binding the excess mineral acid. The arestuff separating from the solution is filtered off and washed. When dried it represents a red powder, dissolving in concentrated sulfuric acid with red-violet coloration.

We claim:---

1. As new products water-insoluble azo dyestuffs of the general formula:

OHaO HO HNO 0 N-OgS OOH; It:

OHaO H0 HNOC- wherein R1 and R2 stand for alkyl groups together containing three to eight carbon atoms, "said products being generally red powders, and

yielding when prepared on the fiber generally wherein R1 stands for alkyl containing from one to four carbon atoms, Rz stands for benzyl, said products being generally red powders, and yielding when prepared on the fiber generally Turkey red shades of good Iastness properties.

Turkey red shades of good fastness properties.

3. As new products water-insoluble azo dyestuffs of the general formula:

II N wherein R1 stands for alkyl containing from one to four carbon atoms, R2 stands for alkyl containing from two to four carbon atoms, said products being generally red powders, and yielding when prepared on the fiber generally Turkey red shades of good fastness properties.

4. As a new product a water-insoluble azo dyestuff of the formula:

/NO:S OCHt H50;

N ll 01 N HNO 0 said product being a red substance, yielding when prepared on the fiber a Turkey red shade of good fastness properties.

5. As a new product-a water-insoluble azo dyei 15 stuff of the formula:

' N-o,s -oom mo-Eo-mo-mo i 01 it HNOO said product being a red substance, yielding when prepared on the fiber a. Turkey red shade of good fastness properties.

6. As new products water-insoluble azo dyestufis of the general formula:

N-OgSQO CH; B: in 01 N omo no HNOO 7. As a new product a water-insoluble azo dyestuff of the formula:

N-0:S 0 CH 11509-1120 N H 01 N OHaO HO- HNO C said product being a red substance, yielding when prepared on the fiber a Turkey red shade of good fastness properties. 

